Synthesis and antifungal activity of (-)-(Z)-dysidazirine.
A short, flexible synthesis of the marine natural product (2 R)-(Z)-dysidazirine (-)-1 has been completed. (-)-1 shows significant antifungal activity across a panel of seven human pathogens, whereas the structural analogue (-)-2, featuring a terminal tert-butyl group, is essentially inactive.
Skepper
Colin K
CK
Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, California 92093, USA.
Dalisay
Doralyn S
DS
Molinski
Tadeusz F
TF
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects; D013237:Stereoisomerism
D000935:Antifungal Agents; D001389:Azirines; C096952:dysidazirine